The Great Talbot County Loop: An Introduction
For generations, travelers have arrived in the nation’s capital to explore and savor a uniquely American city. After a few days of patriotic fun, they amble into the countryside to find the yin to D.C.’s big city yang, making a loop around the Chesapeake Bay through rural Maryland and Virginia.
Talbot County occupies a place of honor along that well-trodden path, hugging the edge of the Chesapeake Bay like a child embracing its mother. It’s here, on the Great Talbot County Loop, that you’ll find the best of the Chesapeake culture and cuisine, much of it bound together by a ribbon of backroads that string together the small-town pearls of Easton, Oxford, and St. Michaels. A 13-mile sidetrack puts you in an authentic working waterman’s village.
Each town within the Great Talbot County Loop offers its own distinct character and timeless appeal. Each serving as a vibrant stop on this loop tour, creating a journey that whispers tales of colonial grandeur, maritime heritage, and the tranquil beauty of the Chesapeake Bay.
Explore the Great Talbot County Loop
Cruisin’ the Great Talbot County Loop: Stop 1 – Easton
Easton is as sophisticated as it is lively. Featuring a worldclass theater, renowned art galleries, and impeccably curated museums, Easton is the heart of the Eastern Shore’s arts and culture scene.
Cruisin’ the Great Talbot County Loop: Stop 2 – Oxford
The picture-perfect town of Oxford offers a graceful waterfront and is home to brick-lined streets anchored by history and great restaurants.
Cruisin’ the Great Talbot County Loop: Stop 3 – St. Michaels
Nestled along the Miles River, St. Michaels is a historic waterfront town that’s home to museums and boutiques, gourmet restaurants and crab shacks, and plenty of adventure by land or by sea.
Cruisin’ the Great Talbot County Loop: Stop 4 – Tilghman Island
Route 33 South takes you to the quintessential historic American waterfront village of Tilghman Island. This 20-minute drive is an experience unto itself. Just off the beaten path, Tilghman Island is nestled between the Chesapeake Bay and the Choptank River.
